Hydroxy substituted unsaturated acids and esters and derivatives thereof

ABSTRACT

ALIPHATIC ACIDS AND ESTERS HAVING A BACKBONE OF AT LEAST 12 CARBON ATOMS LOWER ALKYL AT C-3, C-7, AND C-11 UNSATURATION AT C-2,3 AND SUBSTITUTED AT C-11 OR C-7,11 WITH HYDROXY AND ESTERS AND ETHERS THEREOF WHICH ARE USEFUL ARTHROPOD MATURATION INHIBITORS.

United States Patent HYDROXY SUBSTITUTED UNSATURATED ACIDS AND ESTERSAND DERIVATIVES THEREOF John B. Siddall, Palo Alto, Calif., and JeanPierre Calame,

Locarno, Switzerland, assignors to Zoecon Corporation, Palo Alto, Calif.

No Drawing. Application July 22, 1969, Ser. No. 843,818, now Patent No.3,671,558, dated June 20, 1972, which is a continuation-in-part ofapplication Ser. No. 800,266, Feb. 18, 1969, which is acontinuation-in-part of application Ser. No. 618,351, Feb. 24, 1967,which in turn is a continuation-in-part of application Ser. No. 590,195,Oct. 29, 1966, all now abandoned. Divided and this application Mar. 19,1971, Ser. No. 126,298

Int. Cl. A01n 9/24; C07c 59/18, 69/66 US. Cl. 260-405 20 Claims ABSTRACTOF THE DISCLOSURE Aliphatic acids and esters having a backbone of atleast 12 carbon atoms lower alkyl at C-3, C-7, and 0-11 unsaturation atC-2,3 and substituted at C-ll or C7,11 with hydroxy and esters andethers thereof which are useful arthropod maturation inhibitors.

CROSS REFERENCE This is a division of Ser. No. 843,818, filed July 22,1969, now US. Pat. 3,671,558, issued June 20, 1972, which is acontinuation-in-part of Ser. No. 800,266, filed Feb. 18, 1969, nowabandoned, which is a continuation-in-part of Ser. No. 618,351, filedFeb. 24,

1967, now abandoned, which is a continuation-in-part of Ser. No.590,195, filed Oct. 29, 1966, now abandoned.

INCORPORATION BY REFERENCE Reference is hereby made to US. Pat.3,671,558. All description therein is incorporated herein by reference.

SUMMARY OF INVENTION Hydroxy substituted long chain aliphatic acids andesters are prepared by hydroxylation of a 2,10-di-unsaturated or2,6,10-tri-unsaturated acid or ester. The hydroxy group is at positionC-ll or C-7 and 0-11. The hydroxy group is converted to thecorresponding ether or ester. The compounds are useful as insectmaturation inhibitors.

What is claimed is:

1. A compound of the following formula:

Bee CH e 8- I in which, Z is hydroxy, acetoxy or lower alkoxy; each of RR R and R is methyl or ethyl; and R is hydrogen or lower alkyl.

2. A compound according to Claim 1 wherein Z is hydroxy and R is loweralkyl.

3. A compound according to claim 1 wherein Z is hydroxy; each of R R Rand R is methyl and R is methyl or ethyl.

4. A compound according to claim 1 wherein Z is lower alkoxy and R islower alkyl.

5. A compound according to Claim 1 wherein Z" is methoxy or ethoxy.

6. A compound according to Claim, 5 wherein Z is ethoxy; each of R R Rand R is methyl and R is ethyl,

3,819,667 Patented June 25, 1974 ice in which, R is hydrogen or loweralkyl; each of R R, R and R is methyl or ethyl; and Z is hydroxy,acetoxy or lower alkoxy.

11. A compound according to Claim 10 wherein Z is hydroxy and R is loweralkyl.

12. A compound according to Claim 10 wherein Z is hydroxy; each of R R Rand R is methyl and R is methyl or ethyl.

13. A compound according to Claim 10 wherein Z is lower alkoxy and R islower alkyl.

14. A compound according to Claim 10 wherein Z is methoxy or ethoxy andR is lower alkyl.

15. A compound according to Claim 14 wherein each of R R R and R ismethyl.

16. A compound according to Claim 15 wherein R is methyl or ethyl.

17. A compound according to Claim 10 wherein Z is acetoxy and R is loweralkyl.

18. A compound according to Claim 17 wherein each of R R R and R ismethyl and R is methyl or ethyl.- 19. A compound of the followingformula:

FOREIGN PATENTS 675,262 12/1963 Canada.

OTHER REFERENCES Bowers et al.: Life Sciences, vol. 4, pp. 2323-31(1965').

Mikhailov et al.: Izvest. Akad. Nauk S.S.S.R., Otdel. Khim. Nauk, 1960,935-6, May 1960.

LEWIS GO'ITS, Primary Examiner D. G. RIVERS, Assistant Examiner US. Cl.X.R.

2604l0.9 R, 413; 424--Dig. 12

UNITED STATES PATENT OFFICER CERTIFICATE OF CORRECTION Paten 3,819,667Dated June 25, 1974 Inventor(s) John B. Siddall and Jean Pierre CalameIt is certified that error appears in the above-identified patent andthat said Letters Patent are hereby corrected as' shown below:

Claim 10, that part of the formula appearing as 2 "-C --CH should read-C=CH Signed and sealed this 24th day of September 1974.

(SEAL) Attest:

McCOY M. GIBSON JR. c. MARSHALL DANN I Commissioner of Patents AttestingOfficer USCOMM-DC 60376-P69 w u.s. GOVERNMENT PRINTING OFFICE: 19690-366-334 F ORM PO-105O (10-69)

